反応 #82739

反応方程式

methylene chloride ether

ethyl ether hexane

water

(-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid

→

title compound

収率 99.0%

(-)-4-(3-Cyanophenyl)-2-trifluoromethyl-4,6,7,8-tetrahydro-5 (1H)-quinolone

収率 99.0%

溶媒

N-methylpyrrolidin-2-one

反応条件

後処理

1. 1
   その他The cooled reaction mixture
2. 2
   抽出extracted twice with ethyl ether
3. 3
   洗浄The combined ether extracts were washed twice with water
4. 4
   乾燥dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   その他the solvent removed
7. 7
   その他to yield an off-white solid

実験手順

A stirred solution of (-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (3.93 g, 10.85 mmol) in N-methylpyrrolidin-2-one (24 mL) was placed in a preheated oil bath at 210° C. for 20 minutes. The cooled reaction mixture was then poured into water (200 mL) and extracted twice with ethyl ether. The combined ether extracts were washed twice with water, dried (MgSO4), filtered and the solvent removed to yield an off-white solid. Chromatography (eluent: methylene chloride/ether 9:1) and trituration with ethyl ether/hexane provided the title compound (3.42 g, 79%) as a white solid mp 187°-189° C. NMR: 1.88-1.91 (m,2H, CH2), 2.21-2.25 (m,2H, CH2), 2.53-2.64 (m,2H, CH2), 4.68(d,1H, J=5.3 Hz, CH), 5.61 (d,1H, J=5.3 Hz, CH), 7.50-7.54 (m,2H, Ar), 7.61-7.66 (m,2H, Ar), 9.42 (s,1H, NH); MS: m/z=319(M+1); [α]D23 =-606.8° (c=0.665 methanol). Analysis for C17H13F3N2O: Calculated: C, 64.14; H, 4.12; N, 8.80; Found: C, 64.07; H, 4.24; N, 8.78.

出典